Dimethylformamide → 1,4-Bis(tert-butoxycarbonyl)-2-[2-(2-oxo-1,3-oxazolan-3-yl)ethyl]piperazine
Reaction equation
[H-].[Na+].[O:3]1[CH2:7][C:6](=O)[N:5]=[C-:4]1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH:17]1[CH2:29][CH2:30]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:15])([CH3:12])([CH3:11])[CH3:10].CN(C)C=[O:45]>>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH:17]1[CH2:29][CH2:30][N:5]1[CH2:6][CH2:7][O:3][C:4]1=[O:45])=[O:15])([CH3:12])([CH3:11])[CH3:10]Participants
5
Conditions
- Temperature
- 90 °C
Procedure
To a suspension of sodium hydride (60%, 57 mg) in N,N-dimethylformamide (20 ml), 2-oxazolidone (0.122 g) was added, followed by stirring at 90° C. for 1 hour. A solution of 1,4-di(tert-butoxycarbonyl)-2-(2-tosyloxyethyl)piperazine (0.686 g) in N,N-dimethylformamide (15 ml) was added to the reaction mixture. The resulting mixture was stirred at 90° C. for 4 hours. The reaction mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with water and saturated aqueous NaCl solution, dried over magnesium sulfate and concentrated under reduced pressure, whereby the title compound (0.515 g) was obtained as a colorless solid.
Workup
- additionwas added
- stirringThe resulting mixture was stirred at 90° C. for 4 hours
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionThe residue was diluted with ethyl acetate
- washwashed with water and saturated aqueous NaCl solution
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure, whereby the title compound (0.515 g)
- customwas obtained as a colorless solid
Sources & evidence
- ORD record
- ord-59807eee1f5342afa1c3ee2d39fe6bea
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06747023B1
Reaction notes
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